So as I've been training at my job the past few months, I've been having to drive to meet at my coworkers house. Was running a bit later than my usual lateness one day, spilt my coffee on me, but got to my coworkers place. Hopped in company vehicle, threw it in reverse and slam. His girlfriend, who is usually gone at that time, was indeed not gone, and I hit her car, leaving a nasty dent in the door. My coworker exclaiming "Mann, I was just getting ready to sell that! It didn't have a dent in it! It's a special 40th anniversary paint job!!"

We get on with our day.. He says some stuff like "I think I saw one like it in this junk yard, but I don't remember if it was a 2 door or 4 door, and either way it'll have to be repainted since the paint isn't going to be worn the same."

Car is an 02 Grand Prix. He was ready to sell it for $2,500. At first we weren't going to tell the company, or at least, weren't sure if we should. 4-5 hours pass and he takes it upon himself to see what they will say, maybe their insurance will just cover it.

Well, in the brief phone call the boss/owner's wife said that if they make a claim that I may be taken off the insurance. My driving record is otherwise clean (I'm 28, had an accident at 16 and didn't drive/have insurance from ~20-25yo). That's as far as we got with it that day, my coworker leaving me with "well figure out what ya wanna do"

I should mention here too, that my coworker had suggested that as the damages would be $1,000 , that I may as well just buy the car from him, as that way I will have something instead of just losing a grand or more. I admit, that as my jeep liberty has nearly 220,xxx miles, that the grand prix with 160,000 might be a smart choice, however, I've been depleting my savings ever since making this career change ~8 months ago, and $2,500 would be 80% of what I have left. Anyways...

Next day, we meet at the shop, no more meeting at my coworkers (thank god as I'm saving myself 40 miles of gas). Dreadfully await coworkers arrival. He arrives, boss comes out and observes van.
"What did you do!?" Bossman says,
"I know... :/"
"Nah I'm just messin', we'll figure it out."
Coworker and I go on with our day. End of the day I'm getting my stuff from his van and he says "well alright, think about what you want to do over the weekend"

So then I'm confused.. as I thought what bossman had said meant insurance would cover it. So over the weekend I'm discussing it with people, and my mechanic buddy sent me a link to what seems to be the same car, only 60 miles away, 0 damage, presumably same color, $100 for the door. I get excited and try to make a plan to shoot out there before they closed at noon on Saturday, before realizing I probably can't get a door off myself and I'm not sure about,, a lot.

So now it's Monday. I get to the shop. I see boss man. "How was your weekend?" He asks me. "Alright I guess.." I tell him, and tell him about how our work app glitched and didn't clock me out on Friday. We go about our work day, no mention about the situation with bossman.

20 minutes into our drive my coworkers asking me what I want to do. I was still half asleep which is why I hadn't brought it up by then too. But I told him we should all sit down and think about the options. Would I get taken off the insurance? How much is the deductible? How much would it cost to fix at a body shop? My coworker was worried his homeowner's insurance would go up but he called real quick and found out that wouldn't be the case. Lots of people say that the company covers it, period. I was clocking in (not clocked in as I had to redownload work app). My sister who is a lawyer suggested I just pay for it out of pocket, which as I mentioned, would be the rest of my savings. I also have an epileptic dog (diagnosed ~8months ago) and like to have emergency funds for his needs..

So.. Last part of this story, and where I get even more confused. My mechanic friend has been dating a girl who does body work, and they even did their whole garage to be able to paint with vent hoods and all. He said if I bring him the door, she can paint it the right color. Excited, I tell my coworker thinking I found the solution. $100 for the door, and whatever my buddy wants, maybe $200 or something. Well, this motherfucker says something like "Well, if the repairs are gonna cost $600, maybe I'd just sell it for $1,900 as is and take the $600 to put towards another car"

He also said "Oh but then my girlfriend won't have a car while they're painting it, well,, maybe if it was on the weekend,, I don't know how long it takes or nothing"

I'm just confused. Like what does that mean? I found the perfect solution. He had made no mention of selling the car as is before I suggested that. All he would repeat was how there wasn't a dent on it before and blah blah 40th anniversary. I almost think he just wants me to get fucked, or to try and get max repair costs from me, (or from insurance if we go that route, just crossed my mind too..) But yeah, anybody have any advice? I think I need to bring it up to bossman, but I'm just confused. Right now he has pictures sent to a body shop to recieve a quote, which they should call back either tonight or tomorrow. But one thing I just realized while typing this is, if he had mentioned the car not being available to his girlfriend while my buddy paints the door right, then what does he expect a body shop to do!?

This is stressing me all out and has got my mind spinning in circles. Any advice would be greatly, greatly appreciated. It feels like ever since embarking on this new career adventure everything has just been crumbling around me. Everything is getting so expensive and I'm making a decent amount less than I did at my previous job (bar food cook). Ugh. Thanks for reading this if you made it through. Thanks is advance for any sort of advice.